Own Your Own Career, Ask Yourself What You Want and Be Curious: Career Advice From a VP

Sponsored by The Hanover Insurance Group

Amy Mass

Photo courtesy of The Hanover Group.

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“The energy and empowering culture that we’ve built is the product of commitment and consistency,” Amy Mass says of The Hanover Insurance Group. “It’s become a very special place to grow and truly thrive.”

This is certainly true for Mass herself. The Vice President and Group Counsel, Office of the General Counsel transitioned into her current role just over a year ago and has already seen significant growth. “I’m learning so much about areas outside my expertise, and I find that fascinating,” she says. “I delight in digging into any project, but I’ve learned it’s not just about operational excellence. Developing as a leader is a long game, involving learning to look ahead and around the corner and applying your experience, judgment and insight to help others see core issues and make sound decisions to advance the strategy.

Mass notes that she’s always loved being part of something bigger and, in her current role, she’s been given “an even greater opportunity to work with strong leaders in different areas of the business to coalesce around our shared vision for the company.”

In this interview, Mass discusses The Hanover’s culture of learning, her best advice on leadership and how to “own your career.”

Tell us about your current and previous role.

In my previous role, I provided legal advice to our field leadership team for 50% of the states where we write personal and commercial lines of insurance. I was responsible for regulatory and government affairs in my region, particularly Michigan, and was heavily involved in national and state trade associations to support a public policy environment that enables the property and casualty insurance industry to deliver the best products and services.

Now, I lead that same team of lawyers, and my responsibilities are similar in some ways but are quite different overall. I still provide legal, regulatory and public policy advice but in an enterprise-wide, strategic business partnership with more senior leaders. 

Leading my team is less about daily involvement in the subject matter and more about understanding the impact of that work and finding ways to enhance the value that our team delivers to our business partners. Joining the company’s Senior Leadership Team affords me more opportunities to collaborate on vision and strategy. 

I’m relocating to Worcester, Massachusetts, where the majority of my team is based. Despite the value we’ve all discovered during our remote work arrangements with video and other technology tools, I’m looking forward to some level of in-person connection.

What, specifically, helped lead to this promotion?

I know it was more than working hard to get the job done. Consistent daily performance built and refined my expertise, but I also get excited about opportunities for leadership and networking with talented and terrific people whom I genuinely enjoy and can learn something new from every day. Building relationships within the company and my industry was important, but rounding that out with diverse experiences and relationships was, in my opinion, what led me to be more curious, learn about the world in which the company operates and think more innovatively.

With that as a backdrop, when I had the chance to lead through a major legislative initiative in Michigan that sought to change significant portions of the insurance code, I put that experience to the test. I had previously worked with internal and external partners to educate various constituencies about the mechanisms of the no-fault insurance system, why it had become unaffordable for many consumers and how it was unsustainable in its current form. As we were advocating for and anticipating legislative change, I worked within my company to collaborate with key leaders as we planned for change, even though we didn’t know exactly what that would look like. 

 Once the laws were passed — some of which we had anticipated and others of which were surprises — we had to work internally to implement the changes and externally to negotiate the new regulatory and customer-facing environment. It touched virtually every area of our company and was a monumental change to the business of selling private passenger automobile insurance to our largest customer base and in partnership with our largest network of independent agent partners. 

The intensity was fierce, but having the chance to lead — drawing on my legal experience, analytical skills, practical judgment, business partnerships and strong relationships — was a tremendous opportunity to navigate change with composure, resilience and a lot of good humor.   

What advice do you have to others in your industry who want to take their career path to the next level?

Ask!  But not in the way that you might think. Yes, it’s important to make it known that you’re interested in advancement, but it can’t be for the sake of title, money or gravitas — or even just because you think that’s what you’re “supposed to do.” Actions speak louder than words, so definitely have those conversations, but back it up by investing in yourself, showing up with consistent performance and really thinking about why it is you want to advance. 

Do you know what the “next step” job is, and do you really want to do it? If not, there’s so much joy to be found in doing what you love and continuing to “grow in place,” in your current role or maybe a lateral move. If you do really want that “next level up,” there are more questions to ask.  What are you passionate about? What can you contribute beyond just your experience and subject matter knowledge? Where do you need to grow and develop in order to thrive as a leader? And what’s the bigger picture? 

“Next level” can mean moving up, but it can also mean advancing your skills and broadening your horizons with new challenges in your current role or a slightly different path. There’s more than one “next level,” and if you genuinely embrace the journey, you’ll reach the destination.

What’s the first thing you do at work every day? 

I scan my email, headlines and industry and non-industry news and find something inspiring to read when I can. There’s so much to stay on top of, and though I can never digest it all, I need some familiarity with current events.

What’s your favorite career mistake that you’ve made? 

Trying to be all things to all people. You can’t do it all, and you can’t be it all — or, at least, I couldn’t. Learning that (through some cringe-worthy missteps) was an important career and life lesson. Early in my career, I thought I was supposed to follow a certain path — partner track at a law firm with glamorous cases and a social circle that would help develop clients and further my career. My generation was inspired by L.A. Law! In reality, I felt a lot more like Ally McBeal.

Initially, I felt like I failed when I discovered it wasn’t right for me. But then I searched for and found what I loved to do and talented, trustworthy people to do it with, and everything changed. The hard work became energizing, and I was excited to grow and develop in ways that I never even imagined.

What’s the most memorable piece of career advice you’ve received?  

Own your own career. More recently, I’ve heard it phrased as “Be the CEO of your career.”  Seek out development opportunities, build meaningful, diverse relationships both within and outside of your industry and your peer group, advocate for yourself and mentor/sponsor others.  There are many ways to chart your career path, but no one will hand it to you on a silver platter, no matter how deserving you are.  


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